US5292500A - Plaque-inhibiting toothpaste comprising antibacterial biguanides - Google Patents

Plaque-inhibiting toothpaste comprising antibacterial biguanides Download PDF

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Publication number
US5292500A
US5292500A US07/835,920 US83592092A US5292500A US 5292500 A US5292500 A US 5292500A US 83592092 A US83592092 A US 83592092A US 5292500 A US5292500 A US 5292500A
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US
United States
Prior art keywords
weight
fatty acid
toothpaste
partial esters
ethoxylated fatty
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Expired - Fee Related
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US07/835,920
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English (en)
Inventor
Peter Wuelknitz
Rudolf Lehmann
Walter Ploeger
Franz Foerg
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Assigned to HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN (HENKEL KGAA) A CORP. OF THE FED. REP. OF GERMANY reassignment HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN (HENKEL KGAA) A CORP. OF THE FED. REP. OF GERMANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: FOERG, FRANZ, LEHMANN, RUDOLF, PLOEGER, WALTER, WUELKNITZ, PETER
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26Aluminium; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/43Guanidines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters

Definitions

  • This invention relates to a toothpaste in the form of a dispersion of water-insoluble polishing agents in an aqueous carrier which contains an antimicrobial biguanide compound as plaque-inhibiting component and of which the other components are selected in regard to type and quantity so that optimal inhibition of plaque formation is obtained despite a relatively low dosage of the antimicrobial biguanide compounds.
  • antimicrobial biguanide compounds are effective in inhibiting the formation of plaque.
  • their effect in this regard is greatly reduced or totally eliminated by many components typically present in toothpastes, more particularly by certain polishing agents, by many binders or consistency regulators, surfactants and even by sweeteners.
  • the present invention relates to a toothpaste in the form of a dispersion containing
  • additives from the group consisting of surfactants, flavoring oils and sweeteners,
  • nonionic polysaccharide derivatives as consistency regulators
  • flavouring oil an alkyl glycoside and optionally a nonionic solubilizer for the flavouring oil as surfactants and
  • ⁇ -Aluminum oxide trihydrate, Al (OH) 3 is a known polishing agent for toothpastes.
  • a ground quality in which the particles are predominantly (at least 98%) smaller than 50 ⁇ in size with an average of approximately 1 to 10 ⁇ is particularly suitable.
  • the toothpaste according to the invention preferably contains a mixture of ⁇ -aluminium oxide trihydrate (A) and a weakly calcined alumina (B) in a ratio by weight of A to B of 100 : (1-15) in a quantity of 30 to 604 by weight, because a particlularly good polishing effect with no roughening secondary effect is obtained in this way.
  • A ⁇ -aluminium oxide trihydrate
  • B weakly calcined alumina
  • the weakly calcined alumina preferably has a gamma-aluminium oxide ( ⁇ -Al 2 O 3 ) content of approximately 20% by weight and an alpha-aluminium oxide ( ⁇ -Al 2 O 3 ) content of approximately 80% by weight, an agglomerate size below 20 ⁇ , an average primary crystal size of 0.5 to 1.5 ⁇ and an apparent density of 500 to 600 g/l.
  • ⁇ -Al 2 O 3 gamma-aluminium oxide
  • ⁇ -Al 2 O 3 alpha-aluminium oxide
  • Suitable weakly calcined aluminas are obtained by calcination from aluminium hydroxide. Aluminium hydroxide is converted by calcination into ⁇ -Al 2 O 3 which is thermodynamically stable at temperatures above 1,200° C.
  • the thermodynamically unstable forms of Al 2 O 3 occurring at temperatures between 400° and 1,000° C. are known as gamma forms (cf. Ullmann, Encyclopadie der ischen Chemie, 4th Edition (1974), Vol. 7, page 298).
  • the degree of calcination i.e. the conversion into the thermodynamically stable ⁇ -Al 2 O 3 , can be adjusted as required through the calcination temperature and the calcination time.
  • Weakly calcined aluminas are distinguished from pure ⁇ -Al 2 O 3 by lower agglomerate hardness, a larger specific surface and larger pore volumes.
  • Aluminium oxide polishes are commercially available in various degrees of calcination, fineness and apparent density, as for example the “Poliertonerden (Polishing Aluminas)" of Giulini Chemie.
  • humectants used include glycerol, sorbitol, propylene glycol and polyethylene glycols; glycerol and/or sorbitol are preferred.
  • Suitable water-soluble consistency regulators are the nonionic polysaccharide derivatives, for example methyl, hydroxyethyl and hydroxypropyl ethers, of cellulose, starch, guar and vegetable gums. Hydroxyethyl cellulose and methyl hydroxypropyl cellulose are preferably used.
  • chlorhexidine 1,1'-hexamethylene bis- [5- (4-chlorophenyl) -biguanide]
  • chlorhexidine known from GB-A-705,838 in the form of a water-soluble, physiologically compatible salt, for example in the form of the acetate or gluconate, is preferably used as the antimicrobial biguanide compound.
  • antimicrobial biguanide compounds suitable for use in accordance with the invention are, for example, 1,1'-hexamethylene bis-[5-(4-fluorophenyl)-biguanide] (fluorhexidine) the polyhexamethylene biguanide compounds of the Vantocil® IB (ICI) type known from GB-A-702,268 and also the antimicrobial biguanide compounds known from U.S. Pat. Nos. 2,684,924, 2,990,425, 3,468,898, 4,022,834, 4,053,636 and 4,198,392.
  • Nonionic surfactants of the alkyl glycoside type are used as surfactants in the toothpastes according to the invention.
  • Alkyl glycosides, their production and their use as surfactants are known, for example, from U.S. Pat. Nos. 3,839,318, 3,707,535, 3,547,828, DE-A-19 43 6891 DE-A-20 36 472 and DE-A-30 01 064 and from EP-A-77 167. They are prepared in particular by reaction of glucose or oligosaccharides with primary C 8-16 alcohols.
  • both monoglycosides in which a cyclic sugar residue is attached to the fatty alcohol by a glycoside bond and oligomeric glycosides having a degree of oligomerization (OG) of preferably up to 3 are suitable.
  • Preferred alkyl glycosides for the production of the preparations according to the invention are those containing 8° to 18° C. atoms in the alkyl group and having an average degree of oligomerization of the glycoside residue of 1 to 3.
  • the degree of oligomerization (OG) is a statistical mean value based on a homolog distribution typical of such industrial products.
  • the alkyl glycosides are preferably present in the toothpaste according to the invention in quantities of 0.025 to 2.5% by weight.
  • the organoleptic properties of the toothpaste according to the invention can be improved by the addition of flavoring oils and sweeteners.
  • Suitable flavoring oils are any of the natural and synthetic flavors typically used in oral and dental hygiene preparations. Natural flavors may be used both in the form of essential oils isolated from the drugs and in the form of the individual components isolated from the essential oils.
  • the toothpaste should preferably contain at least one flavoring oil from the group consisting of peppermint oil, spearmint oil, anise oil, Japanese anise oil, caraway oil, eucalyptus oil, fennel oil, cinnamon oil, clove oil, geranium oil, sage oil, pimento oil, thyme oil, marjoram oil, basil oil, lemon oil, wintergreen oil or one or more synthetic components of these oils isolated therefrom.
  • at least one flavoring oil from the group consisting of peppermint oil, spearmint oil, anise oil, Japanese anise oil, caraway oil, eucalyptus oil, fennel oil, cinnamon oil, clove oil, geranium oil, sage oil, pimento oil, thyme oil, marjoram oil, basil oil, lemon oil, wintergreen oil or one or more synthetic components of these oils isolated therefrom.
  • oils mentioned are, for example, menthol, carvone, anethol, cineol, eugenol, cinnamaldehyde, caryophyllene, geraniol, citronellol, linalool, salvene, thymol, terpinene, terpineol, methyl chavicol and methyl salicylate.
  • suitable flavors are, for example, menthyl acetate, vanillin, ionone, linalyl acetate, rhodinol and piperitone.
  • a nonionic solubilizer is necessary for solubilizing these mostly water-insoluble flavoring oils.
  • the solubilizers in question belong to the group of surface-active compounds.
  • the present invention also relates to a toothpaste according to the invention containing 0.1 to 0.5% by weight of a flavoring oil and 0.1 to 0.7% by weight of a nonionic solubilizer, preferably from the group consisting of ethoxylated fatty acid glycerides, ethoxylated fatty acid sorbitan partial esters or fatty acid partial esters of glycerol or sorbitan ethoxylates.
  • Solubilizers from the group of ethoxylated fatty acid glycerides comprise above all adducts of 20 to 60 mol ethylene oxide with mono- and diglycerides of linear C 12-18 fatty acids or with triglycerides of hydroxyfatty acids, such as hydroxystearic acid or ricinoleic acid.
  • Other suitable solubilizers are ethoxylated fatty acid sorbitan partial esters, i.e. preferably adducts of 20 to 60 mol ethylene oxide with sorbitan monoesters and sorbitan diesters of C 12-18 fatty acids.
  • Fatty acid partial esters of glycerol or sorbitan ethoxylates i.e. preferably mono- and diesters of C 12-18 fatty acids and adducts of 20 to 60 mol ethylene oxide with 1 mol glycerol or with 1 mol sorbitol, are also suitable solubilizers.
  • the toothpaste according to the invention preferably contains adducts of 20 to 60 mol ethylene oxide with hydrogenated or non-hydrogenated castor oil (i.e. with hydroxystearic acid or ricinoleic acid triglyceride) , with glycerol mono- and/or distearate or with sorbitan mono- and/or distearate as solubilizers for any flavoring oils present.
  • hydrogenated or non-hydrogenated castor oil i.e. with hydroxystearic acid or ricinoleic acid triglyceride
  • glycerol mono- and/or distearate or with sorbitan mono- and/or distearate as solubilizers for any flavoring oils present.
  • Suitable sweeteners are either natural sugars, for example sucrose, maltose, lactose and fructose, or synthetic sweeteners, but preferably nonionic or amphoteric substances.
  • L-Aspartyl-L-phenyl alanine methyl ester commercially available under the name of Aspartame® is particularly suitable as the sweetener.
  • caries-inhibiting agents such as sodium fluoride or sodium monofluorophosphate
  • pigments for example titanium dioxide
  • pH regulators for adjusting a pH value of preferably 6 to 8 and buffers, for example citric acid and salts thereof or phosphoric acid and alkali salts thereof,
  • wound-healing and anti-inflammatory agents such as for example allantoin, urea, azulene and active substances from camomile.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)
  • Steroid Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US07/835,920 1989-08-25 1990-08-16 Plaque-inhibiting toothpaste comprising antibacterial biguanides Expired - Fee Related US5292500A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3928063A DE3928063A1 (de) 1989-08-25 1989-08-25 Belaghemmende zahnpaste
DE3928063 1989-08-25

Publications (1)

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US5292500A true US5292500A (en) 1994-03-08

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Country Status (15)

Country Link
US (1) US5292500A (zh)
EP (2) EP0489049B1 (zh)
JP (1) JPH04507413A (zh)
KR (1) KR920703002A (zh)
CN (1) CN1041382C (zh)
AT (1) ATE114965T1 (zh)
BR (1) BR9007616A (zh)
CA (1) CA2065268A1 (zh)
DE (2) DE3928063A1 (zh)
DK (1) DK0489049T3 (zh)
ES (1) ES2064754T3 (zh)
MY (1) MY107419A (zh)
PT (1) PT95041B (zh)
RU (1) RU2080107C1 (zh)
WO (1) WO1991002513A1 (zh)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995028410A1 (en) * 1994-04-15 1995-10-26 Henkel Corporation Biologically active composition
US5942211A (en) * 1994-07-25 1999-08-24 Warner-Lambert Company Antiseptic dentifrice
WO2001062212A2 (de) * 2000-02-25 2001-08-30 Henkel Kommanditgesellschaft Auf Aktien System bestehend aus treibgashaltigem zahnreinigungsmittel und spender
EP1267814A1 (en) * 2000-03-30 2003-01-02 SmithKline Beecham Corporation Composition
US20030118518A1 (en) * 1999-04-11 2003-06-26 Rainer Hahn Suspension for the treatment of natural hard tissue and method of treatment
US20030206876A1 (en) * 2000-03-30 2003-11-06 Buch Robert Michael Composition
US20040047815A1 (en) * 2000-12-20 2004-03-11 Bonals Ana Torrado Dentifrice product
US20040108593A1 (en) * 2000-06-23 2004-06-10 Nec Corporation Optical circuit in which fabrication is easy
US20090191510A1 (en) * 2005-06-22 2009-07-30 Cao Group, Inc. Periodontal treatment employing applied ultrasonic energy

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3903348A1 (de) * 1989-02-04 1990-08-30 Henkel Kgaa Mund- und zahnpflegemittel mit polysaccharidspaltenden enzymen
DE3927982A1 (de) * 1989-08-24 1991-02-28 Henkel Kgaa Belaghemmende zahnpaste
DE4340015C2 (de) * 1993-11-24 1996-07-04 Henkel Kgaa Verfahren zur Herstellung wasserfreier, rieselfähiger Zuckertensidpulver und deren Verwendung
DE19601155A1 (de) * 1996-01-15 1997-07-17 Henkel Kgaa Zahnpflegemittel
JPH10251131A (ja) * 1997-03-11 1998-09-22 Sunstar Inc 口腔用組成物
TW200611710A (en) * 2004-10-01 2006-04-16 Tsaur Garry Tooth cleaner and applicator packaging
FR2913896B1 (fr) * 2007-03-20 2011-05-20 Agro Ind Rech S Et Dev Ard Nouvelles compositions a base de glycosides d'alkyle, procede pour leur preparation et utilisation comme agent tensioactifs
EP2568024A1 (en) * 2011-09-07 2013-03-13 Basf Se A chemical mechanical polishing (cmp) composition comprising a glycoside
CN102512337B (zh) * 2012-01-10 2013-04-24 广州薇美姿个人护理用品有限公司 一种益晚牙膏和一种益早益晚组合牙膏
JP2014070046A (ja) * 2012-09-28 2014-04-21 Toyobo Co Ltd Pgaイオンコンプレックスを含有する歯科口腔用組成物

Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB702268A (en) * 1949-08-22 1954-01-13 Francis Leslie Rose Polymeric diguanides
GB705838A (en) * 1951-02-05 1954-03-17 Ici Ltd New bactericidal substances
US2684924A (en) * 1951-02-05 1954-07-27 Ici Ltd Nu-chlorophenyldiguanidino compounds
US2990425A (en) * 1956-06-06 1961-06-27 Ici Ltd New biguanide salts
US3468898A (en) * 1966-05-26 1969-09-23 Sterling Drug Inc Bridged bis-biguanides and bis-guanidines
DE1943689A1 (de) * 1968-09-03 1970-03-12 Rohm & Haas Alkyl-Oigosaccharide und ihre Mischungen mit Alkyl-Glucosiden und Alkanolen
DE2036472A1 (de) * 1969-07-24 1971-02-04 Atlas Chemical Industries Ine , WiI mington, Del (VStA) Verfahren zur Herstellung von Glycosid gemischen
DE2126539A1 (de) * 1970-06-04 1971-12-16 Colgate Palmolive Co Mundpflegemittel
DE2158149A1 (de) * 1970-11-27 1972-06-08 Colgate-Palmolive Co., New York, N.Y. (V.St.A.) Zahnreinigungsmittel mit einem Gehalt an l,6-Di-(p-chlorphenyl-biguagiido)hexan
US3707535A (en) * 1969-07-24 1972-12-26 Atlas Chem Ind Process for preparing mono- and polyglycosides
US3839318A (en) * 1970-09-27 1974-10-01 Rohm & Haas Process for preparation of alkyl glucosides and alkyl oligosaccharides
US4022834A (en) * 1972-03-16 1977-05-10 A/S Farmaceutisk Industri Antibacterially active hexamethylene-bis-biguanides
US4053636A (en) * 1976-05-24 1977-10-11 Sterling Drug Inc. Dichlorocyclopropylphenyl bisbiguanide compounds, processes and compositions
US4198392A (en) * 1975-06-23 1980-04-15 The Procter & Gamble Company Oral compositions containing bis-biguanides with reduced staining tendencies
EP0026252A1 (de) * 1979-09-27 1981-04-08 Blendax-Werke R. Schneider GmbH & Co. Mittel zur oralen Hygiene
DE3001064A1 (de) * 1980-01-12 1981-07-16 Basf Ag, 6700 Ludwigshafen Verfahren zur reinigung von alkylglycosiden durch destillative abtennung nicht umgesetzter alkohole
EP0077167A1 (en) * 1981-10-08 1983-04-20 Rohm And Haas France, S.A. A process for preparing surface-active glycosides and the use of the glycosides in cosmetic, pharmaceutical and household products
US4495170A (en) * 1981-04-29 1985-01-22 Tate & Lyle Public Limited Company Sweetening agents containing chlorodeoxysugar
DE3444958A1 (de) * 1984-12-10 1986-06-12 Henkel KGaA, 4000 Düsseldorf Verwendung von alkylglykosiden als potenzierungsmittel in antiseptischen mitteln sowie desinfektions- und reinigungsmittel mit verstaerkter bakterizider wirkung
EP0304627A2 (de) * 1987-07-30 1989-03-01 Henkel Kommanditgesellschaft auf Aktien Antimikrobiell wirksame, aromatisierte Zubereitungen
US5145665A (en) * 1989-02-04 1992-09-08 Henkel Kommanditgesellschaft Auf Aktien Preparation for dental and oral hygiene containing polysaccharide splitting enzymes

Patent Citations (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB702268A (en) * 1949-08-22 1954-01-13 Francis Leslie Rose Polymeric diguanides
GB705838A (en) * 1951-02-05 1954-03-17 Ici Ltd New bactericidal substances
US2684924A (en) * 1951-02-05 1954-07-27 Ici Ltd Nu-chlorophenyldiguanidino compounds
US2990425A (en) * 1956-06-06 1961-06-27 Ici Ltd New biguanide salts
US3468898A (en) * 1966-05-26 1969-09-23 Sterling Drug Inc Bridged bis-biguanides and bis-guanidines
DE1943689A1 (de) * 1968-09-03 1970-03-12 Rohm & Haas Alkyl-Oigosaccharide und ihre Mischungen mit Alkyl-Glucosiden und Alkanolen
US3547828A (en) * 1968-09-03 1970-12-15 Rohm & Haas Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols
DE2036472A1 (de) * 1969-07-24 1971-02-04 Atlas Chemical Industries Ine , WiI mington, Del (VStA) Verfahren zur Herstellung von Glycosid gemischen
US3707535A (en) * 1969-07-24 1972-12-26 Atlas Chem Ind Process for preparing mono- and polyglycosides
DE2126539A1 (de) * 1970-06-04 1971-12-16 Colgate Palmolive Co Mundpflegemittel
US3839318A (en) * 1970-09-27 1974-10-01 Rohm & Haas Process for preparation of alkyl glucosides and alkyl oligosaccharides
DE2158149A1 (de) * 1970-11-27 1972-06-08 Colgate-Palmolive Co., New York, N.Y. (V.St.A.) Zahnreinigungsmittel mit einem Gehalt an l,6-Di-(p-chlorphenyl-biguagiido)hexan
US4022834A (en) * 1972-03-16 1977-05-10 A/S Farmaceutisk Industri Antibacterially active hexamethylene-bis-biguanides
US4198392A (en) * 1975-06-23 1980-04-15 The Procter & Gamble Company Oral compositions containing bis-biguanides with reduced staining tendencies
US4053636A (en) * 1976-05-24 1977-10-11 Sterling Drug Inc. Dichlorocyclopropylphenyl bisbiguanide compounds, processes and compositions
EP0026252A1 (de) * 1979-09-27 1981-04-08 Blendax-Werke R. Schneider GmbH & Co. Mittel zur oralen Hygiene
DE3001064A1 (de) * 1980-01-12 1981-07-16 Basf Ag, 6700 Ludwigshafen Verfahren zur reinigung von alkylglycosiden durch destillative abtennung nicht umgesetzter alkohole
US4495170A (en) * 1981-04-29 1985-01-22 Tate & Lyle Public Limited Company Sweetening agents containing chlorodeoxysugar
EP0077167A1 (en) * 1981-10-08 1983-04-20 Rohm And Haas France, S.A. A process for preparing surface-active glycosides and the use of the glycosides in cosmetic, pharmaceutical and household products
DE3444958A1 (de) * 1984-12-10 1986-06-12 Henkel KGaA, 4000 Düsseldorf Verwendung von alkylglykosiden als potenzierungsmittel in antiseptischen mitteln sowie desinfektions- und reinigungsmittel mit verstaerkter bakterizider wirkung
US4748158A (en) * 1984-12-10 1988-05-31 Henkel Kommanditgesellschaft Auf Aktien Alkyl glycosides as potentiating agents in antiseptic, disinfecting and cleaning preparations to increase microbicidal activity
EP0304627A2 (de) * 1987-07-30 1989-03-01 Henkel Kommanditgesellschaft auf Aktien Antimikrobiell wirksame, aromatisierte Zubereitungen
US4923685A (en) * 1987-07-30 1990-05-08 Henkel Kommanditgesellschaft Auf Aktien Antimicrobial flavored compositions having particular utility as mouth washes
US5145665A (en) * 1989-02-04 1992-09-08 Henkel Kommanditgesellschaft Auf Aktien Preparation for dental and oral hygiene containing polysaccharide splitting enzymes

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"Poliertonarden (Polishing Aluminas)", Giulini Chemie.
Culminal MHPC, Granulat, 1982. *
Poliertonarden (Polishing Aluminas) , Giulini Chemie. *
Ullmann, Encyklopaedie der technischen Chemie, 4th ed., vol. 7, 1974, p. 298. *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995028410A1 (en) * 1994-04-15 1995-10-26 Henkel Corporation Biologically active composition
US5550115A (en) * 1994-04-15 1996-08-27 Henkel Corporation Biologically active composition
US5942211A (en) * 1994-07-25 1999-08-24 Warner-Lambert Company Antiseptic dentifrice
US20030118518A1 (en) * 1999-04-11 2003-06-26 Rainer Hahn Suspension for the treatment of natural hard tissue and method of treatment
WO2001062212A2 (de) * 2000-02-25 2001-08-30 Henkel Kommanditgesellschaft Auf Aktien System bestehend aus treibgashaltigem zahnreinigungsmittel und spender
WO2001062212A3 (de) * 2000-02-25 2002-02-28 Henkel Kgaa System bestehend aus treibgashaltigem zahnreinigungsmittel und spender
EP1267814A1 (en) * 2000-03-30 2003-01-02 SmithKline Beecham Corporation Composition
EP1267814A4 (en) * 2000-03-30 2003-07-09 Smithkline Beecham Corp PREPARATION
US20030206876A1 (en) * 2000-03-30 2003-11-06 Buch Robert Michael Composition
US20040108593A1 (en) * 2000-06-23 2004-06-10 Nec Corporation Optical circuit in which fabrication is easy
US20040047815A1 (en) * 2000-12-20 2004-03-11 Bonals Ana Torrado Dentifrice product
US20090191510A1 (en) * 2005-06-22 2009-07-30 Cao Group, Inc. Periodontal treatment employing applied ultrasonic energy

Also Published As

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ES2064754T3 (es) 1995-02-01
PT95041B (pt) 1997-04-30
KR920703002A (ko) 1992-12-17
CA2065268A1 (en) 1991-02-26
PT95041A (pt) 1991-04-18
CN1041382C (zh) 1998-12-30
CN1049607A (zh) 1991-03-06
JPH04507413A (ja) 1992-12-24
EP0489049A1 (de) 1992-06-10
ATE114965T1 (de) 1994-12-15
MY107419A (en) 1995-12-30
DE59007951D1 (de) 1995-01-19
EP0414128A1 (de) 1991-02-27
EP0489049B1 (de) 1994-12-07
DK0489049T3 (da) 1995-03-27
BR9007616A (pt) 1992-06-30
WO1991002513A1 (de) 1991-03-07
RU2080107C1 (ru) 1997-05-27
DE3928063A1 (de) 1991-02-28

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